CN112552190A - Novel organic compound and organic light emitting diode including the same - Google Patents

Novel organic compound and organic light emitting diode including the same Download PDF

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CN112552190A
CN112552190A CN202011528666.6A CN202011528666A CN112552190A CN 112552190 A CN112552190 A CN 112552190A CN 202011528666 A CN202011528666 A CN 202011528666A CN 112552190 A CN112552190 A CN 112552190A
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吴炯润
许惠真
魏定纬
陈志宽
金康益
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Ningbo Lumilan New Material Co ltd
Lotting Ltd
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Lotting Ltd
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Abstract

The present invention relates to a novel organic compound and an organic light emitting device including the same. The organic light emitting device exhibits improved driving voltage, light emitting efficiency, light emitting performance, and prolonged lifetime.

Description

Novel organic compound and organic light emitting diode including the same
Technical Field
The present disclosure relates to a novel organic compound and an organic light emitting diode including the same.
Background
Recently, as the size of displays increases, there is an increasing interest in flat display elements that occupy less space. In the art, the technology of organic light emitting displays including Organic Light Emitting Diodes (OLEDs) as flat display elements has been rapidly developed.
The organic light emitting diode realizes light emission by annihilating pairs of holes and electrons generated by injecting holes and electrons from a hole injection electrode (anode) and an electron injection electrode (cathode) into an emission layer interposed between the anode and the cathode. Advantageously, such organic light emitting diodes may be formed on flexible transparent substrates, such as plastic, may be operated at low voltages, consume relatively low power, and have good color reproduction.
Disclosure of Invention
An object of the present disclosure is to provide a novel organic compound that can realize an organic light emitting diode having improved driving voltage, light emitting efficiency, luminance, and extended lifetime.
It is another object of the present invention to provide an organic light emitting diode including the novel organic compound.
The object of the present invention is not limited to the above object. Other objects and advantages of the present disclosure, which are not mentioned above, will be understood from the following description, and more clearly understood through embodiments of the present disclosure. Further, it is easily understood that the objects and advantages of the present disclosure can be achieved by the features disclosed in the claims and the combinations thereof.
In one embodiment of the present disclosure, there is provided a compound represented by the following formula 1:
< formula 1>
Figure BDA0002851564160000021
Wherein, in the formula 1,
R1to R4Is represented by the following formula 2,
R5to R18And R not represented by formula 21To R4Each independently is hydrogen; deuterium; halogen; substituted or unsubstituted C1-C30An alkyl group; substituted or unsubstituted C1-C30Alkyl, wherein one or more methylene groups are substituted by-O-or-S-in such a way that O-or S-atoms are not adjacent; substituted or unsubstituted C2-C30An alkenyl group; substituted or unsubstituted C2-C30Alkenyl in which one or more methylene groups are substituted by-O-or-S-in such a way that no O-or S-atoms are adjacent; substituted or unsubstituted C2-C30An alkynyl group; substituted or unsubstituted C7-C30Aralkyl group; substituted or unsubstituted C6-C30An aryl group; substituted or unsubstituted C2-C30A heteroaryl group; substituted or unsubstituted C3-C30A heteroaralkyl group; substituted or unsubstituted C3-C30A cycloalkyl group; substituted or unsubstituted C3-C30A heterocycloalkyl group; substituted or unsubstituted C3-C30A cycloalkenyl group; substituted or unsubstituted C1-C30An alkylamino group; substituted or unsubstituted C6-C30An arylamino group; substituted or unsubstituted C1-C30Alkoxy or substituted or unsubstituted C6-C30Aryloxy group, provided that R is9To R18Is not CN or nitrile, and R5To R18And R not represented by formula 21To R4Two adjacent groups in (b) may be linked to each other to form a condensed ring,
with the proviso that when all R are excluded9To R18In the case of both of them being hydrogen,
< formula 2>
Figure BDA0002851564160000022
Wherein, in the formula 2,
Ar1and Ar2Each independently is substituted or unsubstituted C1-C30Alkyl, substituted or unsubstituted C6-C30Aryl or substituted or unsubstituted C2-C30Heteroaryl group, Ar1And Ar2May be linked to each other to form a condensed ring.
In one embodiment of the present disclosure, there is provided an organic light emitting diode including an organic layer interposed between a cathode and an anode, wherein the organic layer includes a compound represented by formula 1 above.
In another embodiment of the present disclosure, a product is provided that includes the organic light emitting diode.
The compound represented by the above formula 1 is applied to a material for an organic light emitting diode, and can realize improved driving voltage, light emitting efficiency, light emitting performance, and prolonged lifetime.
Detailed Description
Embodiments of the present disclosure are provided to more fully describe the present disclosure to those skilled in the art. The following embodiments may be modified in various forms. The scope of the present disclosure is not limited to the following embodiments. These embodiments may make the disclosure more thorough and complete, and fully convey the concept of the disclosure to those skilled in the art.
Herein, when two or more groups are simultaneously defined, each group simultaneously defined is independently defined even if not so mentioned. Thus, two or more groups defined simultaneously may be the same or different from each other.
The term "substituted" as used herein means that a hydrogen atom bonded to a carbon atom in a compound is substituted with another substituent. The position at which the substitution occurs may refer to a position at which a hydrogen atom is substituted. That is, the position is not limited to a specific position as long as hydrogen at the position can be substituted by a substituent. When two or more substituents are present, the two or more substituents may be the same or different.
In the present disclosure, the substituent substituting the hydrogen atom may be selected from deuterium, C1-C20Alkyl radical, C1-C20Alkoxy, halogen, cyano, carbonyl, amino, C1-C20Alkylamino, nitro, C1-C20Alkylsilyl group, C3-C30Cycloalkyl silylAlkyl radical, C6-C30Arylsilyl radical, C6-C30Aryl radical, C6-C20Arylamino, C1-C30Heteroaryl group, C1-C30Alkyl, wherein one or more methylene groups are substituted with-O-or-S-in such a way that O atoms or S atoms are not adjacent, and combinations thereof, and is not limited thereto.
As used herein, the term "alkyl" includes any kind of alkyl group, including straight chain alkyl, branched chain alkyl, cycloalkyl, and the like.
As used herein, the term "hetero" in "heteroaromatic ring," "heteroaryl," and the like, unless otherwise defined, at least one carbon, such as 1 to 5 carbons, yet another such as 1 to 4 carbons, yet another such as 1 to 3 carbons, comprising an aromatic ring, aryl, and the like, is substituted with at least one heteroatom selected from N, O, S and combinations thereof.
As used herein, in the definition of substituents, the term "combination thereof" means that two or more substituents are bonded to each other directly or via a linking group, or two or more substituents are condensed with each other.
In one embodiment of the present disclosure, there is provided a compound represented by the following formula 1:
< formula 1>
Figure BDA0002851564160000041
Wherein, in the formula 1,
R1to R4Is represented by the following formula 2,
R5to R18And R not represented by formula 21To R4Each independently is hydrogen; deuterium; halogen; substituted or unsubstituted C1-C30An alkyl group; substituted or unsubstituted C1-C30Alkyl, wherein one or more methylene groups are substituted by-O-or-S-in such a way that O-or S-atoms are not adjacent; substituted or unsubstituted C2-C30An alkenyl group; substituted or unsubstituted C2-C30Alkenyl radicals in which one or more methylene radicalsIs substituted by-O-or-S-in such a way that O atoms or S atoms are not adjacent; substituted or unsubstituted C2-C30An alkynyl group; substituted or unsubstituted C7-C30Aralkyl group; substituted or unsubstituted C6-C30An aryl group; substituted or unsubstituted C2-C30A heteroaryl group; substituted or unsubstituted C3-C30A heteroaralkyl group; substituted or unsubstituted C3-C30A cycloalkyl group; substituted or unsubstituted C3-C30A heterocycloalkyl group; substituted or unsubstituted C3-C30A cycloalkenyl group; substituted or unsubstituted C1-C30An alkylamino group; substituted or unsubstituted C6-C30An arylamino group; substituted or unsubstituted C1-C30Alkoxy or substituted or unsubstituted C6-C30Aryloxy group, provided that R is9To R18Is not CN or nitrile, and R5To R18And R not represented by formula 21To R4Two adjacent groups in (b) may be linked to each other to form a condensed ring,
with the proviso that when all R are excluded9To R18In the case of both of them being hydrogen,
< formula 2>
Figure BDA0002851564160000042
Wherein, in the formula 2,
Ar1and Ar2Each independently is substituted or unsubstituted C1-C30Alkyl, substituted or unsubstituted C6-C30Aryl or substituted or unsubstituted C2-C30Heteroaryl group, Ar1And Ar2May be linked to each other to form a condensed ring.
In one embodiment, the compound represented by formula 1 is represented by formula 1a or formula 1b below:
< formula 1a >
Figure BDA0002851564160000051
< formula 1b >
Figure BDA0002851564160000052
Wherein, in formula 1a and formula 1b,
R9to R18Each independently is hydrogen; deuterium; halogen; substituted or unsubstituted C1-C30An alkyl group; substituted or unsubstituted C1-C30Alkyl, wherein one or more methylene groups are substituted by-O-or-S-in such a way that O-or S-atoms are not adjacent; substituted or unsubstituted C2-C30An alkenyl group; substituted or unsubstituted C2-C30Alkenyl in which one or more methylene groups are substituted by-O-or-S-in such a way that no O-or S-atoms are adjacent; substituted or unsubstituted C2-C30An alkynyl group; substituted or unsubstituted C7-C30Aralkyl group; substituted or unsubstituted C6-C30An aryl group; substituted or unsubstituted C2-C30A heteroaryl group; substituted or unsubstituted C3-C30A heteroaralkyl group; substituted or unsubstituted C3-C30A cycloalkyl group; substituted or unsubstituted C3-C30A heterocycloalkyl group; substituted or unsubstituted C3-C30A cycloalkenyl group; substituted or unsubstituted C1-C30An alkylamino group; substituted or unsubstituted C6-C30An arylamino group; substituted or unsubstituted C1-C30Alkoxy or substituted or unsubstituted C6-C30Aryloxy group, provided that R is9To R18Is not CN or nitrile, and R9To R18Two adjacent groups in (b) may be linked to each other to form a condensed ring,
with the proviso that when all R are excluded9To R18In the case of both of them being hydrogen,
Ar1and Ar2Each independently is substituted or unsubstituted C6-C30Aryl or substituted or unsubstituted C3-C30Heteroaryl radicalAnd Ar1And Ar2May be linked to each other to form a fused ring.
The compound shown in formula 1 can be applied to materials of organic light emitting diodes to improve the efficiency of the organic light emitting diodes.
Holes injected from the anode of the organic light emitting diode reach the emission layer through the hole injection layer and the hole transport layer, and electrons injected from the cathode reach the emission layer through the electron injection layer and the electron transport layer. The holes and electrons injected into the emission layer meet to form excitons to emit light. However, not all of the injected holes and electrons meet in the emission layer, and some of the electrons and holes do not participate in light emission to cause leakage. Hole leakage can be addressed by inserting an appropriate hole blocking layer between the emissive layer and the electron transport layer, or electron leakage can be addressed by inserting an appropriate electron blocking layer between the hole transport layer and the emissive layer. However, since a dopant used as a light emitting material in an emission layer of an organic light emitting device has a property of trapping holes stronger than electrons, it is more effective to prevent leakage of electrons than hole leakage. The compound represented by formula 1 may contribute to improvement of efficiency of the organic light emitting device by preventing electrons, which do not participate in exciton formation in the emission layer, from leaking into the hole transport layer.
In the spiro ring structure of the compound represented by formula 1, the inventors of the present application found that the fluctuation function is separated such that the Highest Occupied Molecular Orbital (HOMO) responsible for the movement of holes is oriented toward the structural portion bonded to the structure of formula 2 and the Lowest Unoccupied Molecular Orbital (LUMO) responsible for the movement of electrons is oriented toward the benzanthracene moiety. The compound of formula 1 is a structure in which the energy levels of HOMO and LUMO are adjusted while minimizing mutual interference of the energy levels of HOMO and LUMO by using the separation fluctuation function phenomenon as described above.
Figure BDA0002851564160000061
By reaction at R9To R18The position of (3) introduces an electron donor, which can increase the LUMO energy to more effectively act as an electron blocking layer. To prevent leakageThe LUMO of the electron blocking layer must be higher than the LUMO of the emission layer (closer to the degree of vacuum) for leakage current. By introducing an electron donor into the benzanthracene group in the structure of chemical formula 1, it can be expected that the LUMO level changes more than the HOMO level. This not only has the effect of preventing electron leakage, but also the electron donating substituent prevents accumulation between benzanthracenes, thereby reducing electron mobility and causing electrons to stay in the emissive layer.
Figure BDA0002851564160000062
Figure BDA0002851564160000071
Specifically, R9To R18At least one of which is methyl, ethyl, isopropyl, t-butyl, phenyl, 4-tolyl, methoxy, ethoxy, propoxy, dimethylamino, methylethylamino, diethylamino, diphenylamino, or phenylmethylamino. By substitution of R11、R12、R14And R17The electrochemical stability can be improved by hydrogen at sites which are regions of the LUMO having a high electron density.
For example, the compound represented by formula 1 may be selected from compounds represented by the following structures:
Figure BDA0002851564160000081
Figure BDA0002851564160000091
Figure BDA0002851564160000101
Figure BDA0002851564160000111
Figure BDA0002851564160000121
Figure BDA0002851564160000131
the compound represented by formula 1 may be used as a material for a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an auxiliary hole transport layer, an emission layer, an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), and the like.
When the compound is used as a material for an organic light emitting device, an organic light emitting device exhibiting improved driving voltage characteristics, light emitting efficiency, luminance, and a prolonged lifetime can be realized while manipulating substituents, and various effects required for the organic light emitting device can be exerted.
In another embodiment of the present disclosure, there is provided an organic light emitting diode including an organic layer interposed between a cathode and an anode, wherein the organic layer includes the compound.
The detailed description of the compound represented by formula 1 is as described above.
Specifically, the organic layer may further include one selected from the group consisting of a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an auxiliary hole transport layer, an emission layer, an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), and a combination thereof according to a desired use.
Each of the organic layers may include a known material that is considered to have a function, or function as the material of the respective layer.
Accordingly, an organic layer selected from the group consisting of a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an auxiliary hole transport layer, an emission layer, an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), and a combination thereof may include the compound represented by formula 1.
Specifically, the organic layer selected from the group consisting of a Hole Transport Layer (HTL), an auxiliary hole transport layer, an emission layer, and a combination thereof may include the compound represented by formula 1. That is, the organic layer including the compound represented by formula 1 is selected from the group consisting of a hole transport layer, an auxiliary hole transport layer, an emission layer, and a combination thereof.
The organic light emitting device may be manufactured by a manufacturing method using a known process. Hereinafter, an exemplary method of manufacturing an organic light emitting device will be described. First, an anode is formed by coating a material for the anode on a surface of a substrate in a conventional manner. The substrate used may be a glass substrate or a transparent plastic substrate having excellent transparency, surface smoothness, easy handling, and water resistance. In addition, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), tin oxide (SnO), which is transparent and has excellent conductivity, may be used2) And zinc oxide (ZnO) as a material of the anode.
Next, a hole injection layer is formed on the surface of the anode by vacuum thermal evaporation or by spin coating by a conventional method. Examples of materials known as hole injection layer materials include copper phthalocyanine (CuPc), 4',4 ″ -tris (3-methylphenylamino) triphenylamine (m-MTDATA), 4',4 ″ -tris (3-methylphenylamino) diphenyl ether (m-MTDAPB), starburst type amine 4,4',4 ″ -tris (N-carbazolyl) triphenylamine (TCTA), 4',4 ″ -tris (N- (2-naphthyl) -N-phenylamino) -triphenylamine (2-TNATA), or IDE406 available from the light emitting company (Idemitsu).
The hole transport layer is formed on the surface of the hole injection layer by vacuum thermal evaporation or spin coating by a conventional method. Examples of materials known as the hole transport layer material include bis (N- (1-naphthyl-N-phenyl)) benzidine (α -NPD), N '-di (naphthalene-1-yl) -N, N' -biphenylbenzidine (NPB), or N, N '-biphenyl-N, N' -bis (3-methylphenyl) -1,1 '-biphenyl-4, 4' -diamine (TPD), and the like.
Alternatively, an auxiliary hole transport layer may be additionally formed between the hole transport layer and the emission layer.
Examples of materials as the hole transport auxiliary layer material are TCTA, tris [4- (diethylamino) phenyl ] amine (tris [4- (diethylamino) phenyl ] amine, N- (biphenyl-4-yl)) -9, 9-dimethyl-N- (4- (9-phenyl-9H-carbazol-3-yl) phenyl) -9H-fluoren-2-amine, tri-p-tolylamine, 1-bis (4- (N, N-di (p-tolylamino) phenyl) cyclohexane (TAPC), MTDATA, mCP, mCBP, CuPC, N ' -bis [4- [ bis (3- (methylphenyl) amino ] phenyl ] -N, N ' -diphenyl- [1,1' -biphenyl ] -4,4' -diamine (DNTPD), TDAPB, and the like.
The emission layer may be formed on the surface of the hole transport layer by vacuum thermal evaporation or spin coating by a conventional method.
When the emissive layer is red, for example, it may include a host material selected from CBP (carbazole biphenyl) or mCP (1, 3-bis (carbazole-9-yl)), and a phosphorescent material including a dopant comprising one selected from: piqir (acac) (bis (1-phenylisoquinoline)) iridium acetylacetonate, PQIr (acac) (bis (1-phenylquinoline) iridium acetylacetonate), PQIr (tris (1-phenylquinoline) iridium), PtOEP (platinum octaethylporphyrin), and combinations thereof; or fluorescent materials including PBD Eu (DBM)3(Phen) or perylene, but not limited thereto.
When the emission layer is green, for example, it may include a host material including CBP or mCP, and may include a phosphorescent material including a dopant material including ir (ppy)3(fac tris (2-phenylpyridine) iridium), or a fluorescent material including Alq 3 (tris (8-hydroxyquinoline) aluminum), but is not limited thereto.
For example, when the emissive layer is blue, it may comprise a host material comprising CBP or mCP, and may comprise a phosphorescent material comprising a dopant material comprising (4,6-F2ppy)2Irpic, or a fluorescent material comprising one selected from: spiro-DPVBi, spiro-6P, Distyrylbenzene (DSB), Distyrylarylene (DSA), PFO-based polymer and PPV-based polymer, but are not limited thereto.
The electron transport layer may be formed on the surface of the emission layer by vacuum thermal evaporation or spin coating by a conventional method. Examples of materials known as materials for the electron transport layer are PBD (2- (4-biphenyl) -5- (4-tert-butylphenyl) -1,3, 4-oxadiazole), TAZ (3- (4-biphenyl) 4-phenyl-5-tert-butylphenyl-1, 2, 4-triazole), spiro-PBD, TPBi (2,2',2- (1,3, 5-benzenetricarballyl) -tris (1-phenyl-1-H-benzimidazole), oxadiazole, triazole, phenanthroline, benzoxazole, benzothiazole, and the like.
The electron injection layer may be formed by vacuum thermal evaporation or spin coating an electron injection layer material on the surface of the electron transport layer in a conventional manner. Examples of materials known as electron injection layer materials may include LiF, Liq, Li2O, BaO, NaCl, CsF, etc.
The cathode may be formed by vacuum thermal evaporation of a cathode material on the surface of the electron injection layer in a conventional manner.
Examples of the cathode material include lithium (Li), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium (Mg), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and the like. In addition, in the case of a top-emission organic light emitting device, Indium Tin Oxide (ITO) or Indium Zinc Oxide (IZO) may be used to form a transparent cathode through which light passes.
When the organic layer is formed by using the compound represented by formula 1, it may also be performed by vacuum thermal evaporation or spin coating.
In another embodiment of the present disclosure, a product is provided that includes an organic light emitting diode according to one embodiment of the present disclosure.
The product can be applied to photoelectricity, medicine, biotechnology, optical fibers, lighting equipment, electrophotographic photoreceptors, photoelectric converters, organic solar cells, switching elements, organic light-emitting field effect transistors, image sensors or dye lasers.
Hereinafter, examples and comparative examples will be explained. Embodiments may be merely examples of the present disclosure. Accordingly, the present disclosure is not limited to the embodiments.
(examples)
Compounds were synthesized as follows according to examples and comparative examples. It should be noted, however, that these examples are provided for illustration only and should not be construed in any way to limit the scope of the present disclosure.
Synthesis example 1
< reaction scheme 1>
Figure BDA0002851564160000161
500ml is filled with N2Into a two-necked flask of (1-A) (9.42g, 20.5mmol), a compound of (1-B) (6.59g, 20.5mmol), sodium tert-butoxide (3.94g, 41.0mmol), tris (dibenzylideneacetone) dipalladium (0) (0.38g, 0.4mmol), a 50% tri-tert-butylphosphine solution (0.38mL, 1.6mmol) and 100mL of toluene were charged, followed by stirring under reflux. After cooling to room temperature, the reaction mixture was cooled with ethyl acetate and H2O extracts the organic layer. The extracted organic layer was over MgSO4Dried and filtered. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography (DCM/hexane) and then recrystallization purification using a DCM/acetone mixed solvent, thereby obtaining compound 1(10.04g, yield: 70%).
MS(MALDI-TOF)m/z:699[M]+
Synthesis example 2
< reaction scheme 2>
Figure BDA0002851564160000162
Compound 2(10.15g, yield: 68%) was obtained in the same manner as in Synthesis example 1, except that Compound 2-A and Compound 2-B were used in place of Compound 1-A and Compound 1-B.
MS(MALDI-TOF)m/z:727[M]+
Synthesis example 3
< reaction scheme 3>
Figure BDA0002851564160000171
Compound 3(10.33g, yield: 75%) was obtained in the same manner as in Synthesis example 1, except that Compound 3-A and Compound 3-B were used in place of Compound 1-A and Compound 1-B.
MS(MALDI-TOF)m/z:699[M]+
Synthesis example 4
< reaction scheme 4>
Figure BDA0002851564160000172
Compound 4(10.65g, yield: 70%) was obtained in the same manner as in Synthesis example 1, except that Compound 4-A and Compound 4-B were used in place of Compound 1-A and Compound 1-B.
MS(MALDI-TOF)m/z:741[M]+
Synthesis example 5
< reaction scheme 5>
Figure BDA0002851564160000181
Compound 5(11.09g, yield: 71%) was obtained in the same manner as in Synthesis example 1, except that Compound 5-A and Compound 5-B were used in place of Compound 1-A and Compound 1-B.
MS(MALDI-TOF)m/z:761[M]+
Synthesis example 6
< reaction scheme 6>
Figure BDA0002851564160000182
Compound 6(11.40g, yield: 73%) was obtained in the same manner as in Synthesis example 1, except that Compound 6-A and Compound 6-B were used in place of Compound 1-A and Compound 1-B.
MS(MALDI-TOF)m/z:761[M]+
Synthesis example 7
< reaction scheme 7>
Figure BDA0002851564160000191
Compound 7(10.47g, yield: 69%) was obtained in the same manner as in Synthesis example 1, except that Compound 7-A and Compound 7-B were used in place of Compound 1-A and Compound 1-B.
MS(MALDI-TOF)m/z:739[M]+
Synthesis example 8
< reaction scheme 8>
Figure BDA0002851564160000192
Compound 8(10.47g, yield: 67%) was obtained in the same manner as in Synthesis example 1, except that Compound 8-A and Compound 8-B were used in place of Compound 1-A and Compound 1-B.
MS(MALDI-TOF)m/z:782[M]+
Synthesis example 9
< reaction scheme 9>
Figure BDA0002851564160000201
Compound 9(11.00g, yield: 71%) was obtained in the same manner as in Synthesis example 1, except that Compound 9-A and Compound 9-B were used in place of Compound 1-A and Compound 1-B.
MS(MALDI-TOF)m/z:755[M]+
Synthesis example 10
< reaction scheme 10>
Figure BDA0002851564160000202
Compound 10(10.62g, yield: 70%) was obtained in the same manner as in Synthesis example 1, except that Compound 10-A and Compound 10-B were used in place of Compound 1-A and Compound 1-B.
MS(MALDI-TOF)m/z:739[M]+
Synthesis example 11
< reaction scheme 11>
Figure BDA0002851564160000211
Compound 11(11.07g, yield: 73%) was obtained in the same manner as in Synthesis example 1, except that Compound 11-A and Compound 11-B were used in place of Compound 1-A and Compound 1-B.
MS(MALDI-TOF)m/z:739[M]+
Example 1
Will have a width of 2X 2cm2Emission area patterned Indium Tin Oxide (ITO) coated glass substrates were thoroughly cleaned, dried, and then treated with oxygen plasma (150W, 5 min, 4X 10)-2Tray). Then, at 3X 10-6And vacuum-depositing each functional layer in turn at a pressure of torr or less to prepare an OLED. Depositing a 10nm thick Hole Injection Layer (HIL) of 1,4,5,8,9, 11-hexaazabenzohexacyanonitrile (HAT-CN) onto a pretreated ITO anode followed by a 60nm thick layer of 4,4' -bis [ N- (1-naphthyl) -N-phenylamino]Biphenyl (NPB) acts as a Hole Transport Layer (HTL). Then, an auxiliary hole transport layer of the above-synthesized compound 1, 95nm thick, was vacuum-deposited on the hole transport layer, and then, a red Emission Layer (EL) 30nm thick was formed by co-depositing 5 wt% of (piq)2ir (acac) as a dopant and CBP as a red host. 35nm thick 2- (4- (9, 10-bis (naphthalen-2-yl) anthracen-2-yl) phenyl) -1-phenyl-1H-benzo [ d]An Electron Transport Layer (ETL) of imidazole (ET1) was formed thereon, and LiF (0.5nm) and Al (100nm) as an Electron Injection Layer (EIL) and a cathode were formed, respectively. Then, in N2A sealing cap including a getter as a UV curing type adhesive is integrated under an atmosphere to protect the OLED from oxygen and moisture in the air, thereby manufacturing the OLED.
Evaluated at 10mA/cm2And by applying 20mA/cm2The life characteristic is measured.
Figure BDA0002851564160000212
Figure BDA0002851564160000221
Examples 2 to 6
An organic light-emitting device was fabricated in the same manner as in example 1, except that compound 2, 3,4, 5 or 6 was used instead of compound 1 as the auxiliary hole-transporting layer.
Comparative examples 1 to 2
An organic light-emitting device was fabricated in the same manner as in example 1, except that compound a or NPB was used instead of compound 1 as the auxiliary hole-transporting layer.
< Compound A >
Figure BDA0002851564160000222
Example 7
Will have a width of 2X 2cm2Emission area patterned Indium Tin Oxide (ITO) coated glass substrates were thoroughly cleaned, dried, and then treated with oxygen plasma (150W, 5 min, 4X 10)-2Tray). Then, at 3X 10-6And vacuum-depositing each functional layer in turn at a pressure of torr or less to prepare an OLED. A 10nm thick Hole Injection Layer (HIL) of 1,4,5,8,9, 11-hexaazabenzohexacyanonitrile (HAT-CN) was deposited onto the pretreated ITO anode, followed by a 60nm thick Hole Transport Layer (HTL) of compound 7. Then, N-bis ([1, 1' -biphenyl) was formed to a thickness of 20nm]-4-yl) -4 '- (9H-carbazol-9-yl) - [1,1' -biphenyl]-4-amine (EB1) was vacuum deposited onto the hole transport layer followed by co-deposition of 5 wt% of N, N-bis (dibenzo [ b, d ] as dopant]Furan-4-yl) -N, N-di-m-tolyl-1, 6-diamine (BD) and 9, 10-di (2-naphthyl) anthracene (BH) as a host form a blue emission layer (EML) 25nm thick. 35nm thick 2- (4- (9, 10-bis (naphthalen-2-yl) anthracen-2-yl) phenyl) -1-phenyl-1H-benzo [ d]Imidazole (ET1) was formed thereon, and LiF (0.5nm) and Al (100nm) as an Electron Injection Layer (EIL) and a cathode were formed, respectively. Then, in N2Under the atmosphereA sealing cap including a getter as a UV curing type adhesive is integrated to protect the OLED from oxygen and moisture in the air, thereby manufacturing the OLED.
Evaluated at 10mA/cm2And by applying 20mA/cm2The life characteristic is measured.
Figure BDA0002851564160000231
Figure BDA0002851564160000241
Example 8
An organic light-emitting device was fabricated in the same manner as in example 7, except that compound 8 was used instead of compound 1 as the auxiliary hole-transporting layer.
Comparative examples 3 to 4
An organic light-emitting device was fabricated in the same manner as in example 1, except that compound B or NPB was used instead of compound 7 as the hole transport layer.
Figure BDA0002851564160000242
< Compound B >
Figure BDA0002851564160000243
Experimental example 1: characterization of OLEDs including an auxiliary hole transport layer
Organic light emitting devices manufactured in examples 1 to 6 and comparative example 1 were analyzed at 10mA/cm2Electro-optical characteristics of the device at an electric current of (1) and at 20mA/cm2Lifetime under current. The results are shown in Table 1 below.
[ Table 1]
Figure BDA0002851564160000251
Figure BDA0002851564160000261
Experimental example 2: performance analysis of OLEDs including hole transport layers
Organic light emitting devices manufactured in examples 7 to 8 and comparative examples 3 to 4 were analyzed at 10mA/cm2Electro-optical characteristics of the device at an electric current of (1) and at 20mA/cm2Lifetime under current. The results are shown in Table 2 below.
[ Table 2]
Figure BDA0002851564160000262
Figure BDA0002851564160000271
The description of the embodiments of the present disclosure is provided to enable any person skilled in the art to make or use the present disclosure. Various modifications to these embodiments will be readily apparent to those skilled in the art. The general principles defined by this disclosure may be applied to other embodiments without departing from the scope of the disclosure. Thus, the disclosure is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.

Claims (10)

1. A compound represented by formula 1:
< formula 1>
Figure FDA0002851564150000011
Wherein, in the formula 1,
R1to R4Is represented by the following formula 2,
R5to R18And R not represented by formula 21To R4Each independently is hydrogen; deuterium; halogen; substituted or unsubstituted C1-C30An alkyl group; substituted or unsubstituted C1-C30Alkyl, wherein one or more methylene groups are substituted by-O-or-S-in such a way that O-or S-atoms are not adjacent; substituted or unsubstituted C2-C30An alkenyl group; substituted or unsubstituted C2-C30Alkenyl in which one or more methylene groups are substituted by-O-or-S-in such a way that no O-or S-atoms are adjacent; substituted or unsubstituted C2-C30An alkynyl group; substituted or unsubstituted C7-C30Aralkyl group; substituted or unsubstituted C6-C30An aryl group; substituted or unsubstituted C2-C30A heteroaryl group; substituted or unsubstituted C3-C30A heteroaralkyl group; substituted or unsubstituted C3-C30A cycloalkyl group; substituted or unsubstituted C3-C30A heterocycloalkyl group; substituted or unsubstituted C3-C30A cycloalkenyl group; substituted or unsubstituted C1-C30An alkylamino group; substituted or unsubstituted C6-C30An arylamino group; substituted or unsubstituted C1-C30Alkoxy or substituted or unsubstituted C6-C30Aryloxy group, provided that R is9To R18Is not CN or nitrile, and R5To R18And R not represented by formula 21To R4Two adjacent groups in (b) may be linked to each other to form a condensed ring,
with the proviso that when all R are excluded9To R18In the case of both of them being hydrogen,
< formula 2>
Figure FDA0002851564150000012
Wherein, in the formula 2,
Ar1and Ar2Each independently is substituted or unsubstituted C1-C30Alkyl, substituted or unsubstituted C6-C30Aryl or substituted or unsubstituted C2-C30Heteroaryl group, Ar1And Ar2May be linked to each other to form a condensed ring.
2. The compound according to claim 1, wherein the compound represented by formula 1 is represented by the following formula 1a or formula 1 b:
< formula 1a >
Figure FDA0002851564150000021
< formula 1b >
Figure FDA0002851564150000022
Wherein, in formula 1a and formula 1b,
R9to R18Each independently is hydrogen; deuterium; halogen; substituted or unsubstituted C1-C30An alkyl group; substituted or unsubstituted C1-C30Alkyl, wherein one or more methylene groups are substituted by-O-or-S-in such a way that O-or S-atoms are not adjacent; substituted or unsubstituted C2-C30An alkenyl group; substituted or unsubstituted C2-C30Alkenyl in which one or more methylene groups are substituted by-O-or-S-in such a way that no O-or S-atoms are adjacent; substituted or unsubstituted C2-C30An alkynyl group; substituted or unsubstituted C7-C30Aralkyl group; substituted or unsubstituted C6-C30An aryl group; substituted or unsubstituted C2-C30A heteroaryl group; substituted or unsubstituted C3-C30A heteroaralkyl group; substituted or unsubstituted C3-C30A cycloalkyl group; substituted or unsubstituted C3-C30A heterocycloalkyl group; substituted or unsubstituted C3-C30A cycloalkenyl group; substituted or unsubstituted C1-C30An alkylamino group; substituted or unsubstituted C6-C30An arylamino group; substituted or unsubstituted C1-C30Alkoxy or substituted or unsubstituted C6-C30Aryloxy group, provided that R is9To R18Is not CN or nitrile, and R9To R18Two adjacent groups in (b) may be linked to each other to form a condensed ring,
with the proviso that when all R are excluded9To R18In the case of both of them being hydrogen,
Ar1and Ar2Each independently is substituted or unsubstituted C6-C30Aryl or substituted or unsubstituted C3-C30Heteroaryl, and Ar1And Ar2May be linked to each other to form a fused ring.
3. The compound of claim 1, wherein R9To R18At least one of which is methyl, ethyl, isopropyl, t-butyl, phenyl, 4-tolyl, methoxy, ethoxy, propoxy, dimethylamino, methylethylamino, diethylamino, diphenylamino, or phenylmethylamino.
4. The compound of claim 1, wherein R11、R12、R14And R17At least one of which is methyl, ethyl, isopropyl, t-butyl, methoxy, phenyl or 4-tolyl.
5. The compound of claim 1, wherein the compound of formula 1 is selected from compounds represented by the following structures:
Figure FDA0002851564150000041
Figure FDA0002851564150000051
Figure FDA0002851564150000061
Figure FDA0002851564150000071
Figure FDA0002851564150000081
Figure FDA0002851564150000091
6. an organic light emitting diode comprising an organic layer between a cathode and an anode, wherein the organic layer comprises the compound of any one of claims 1-5.
7. The organic light emitting diode of claim 6, wherein the organic layer is selected from the group consisting of a hole injection layer, a hole transport layer, an auxiliary hole transport layer, an emissive layer, an electron transport layer, an electron injection layer, and combinations thereof.
8. The organic light emitting diode of claim 6, wherein the organic layer comprising the compound is selected from the group consisting of a hole transport layer, an auxiliary hole transport layer, an emissive layer, and combinations thereof.
9. A product comprising the organic light emitting diode of claim 6.
10. The product according to claim 9, wherein the product is applied in optoelectronics, medicine, biotechnology, optical fibers, lighting devices, electrophotographic photoreceptors, photoelectric converters, organic solar cells, switching elements, organic light emitting field effect transistors, image sensors, or dye lasers.
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114075117A (en) * 2021-06-04 2022-02-22 陕西莱特迈思光电材料有限公司 Organic compound, and electronic element and electronic device using same
WO2023008708A1 (en) * 2021-07-27 2023-02-02 주식회사 로오딘 Organic light-emitting diode

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024136451A1 (en) * 2022-12-20 2024-06-27 주식회사 로오딘 Organic light-emitting diode
WO2024136446A1 (en) * 2022-12-20 2024-06-27 주식회사 로오딘 Organic light emitting diode
WO2024136448A1 (en) * 2022-12-20 2024-06-27 주식회사 로오딘 Novel multifunctional compound and organic light-emitting diode comprising same

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106612616A (en) * 2015-05-08 2017-05-03 陕西莱特迈思光电材料有限公司 Organic electroluminescent device
CN106699573A (en) * 2015-11-17 2017-05-24 材料科学有限公司 Spiro-typed organic materials and organic electroluminescent device utilizing the same
CN110950763A (en) * 2019-11-04 2020-04-03 苏州久显新材料有限公司 Spirobenzanthrone derivatives and electronic devices

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106612616A (en) * 2015-05-08 2017-05-03 陕西莱特迈思光电材料有限公司 Organic electroluminescent device
CN106699573A (en) * 2015-11-17 2017-05-24 材料科学有限公司 Spiro-typed organic materials and organic electroluminescent device utilizing the same
CN110950763A (en) * 2019-11-04 2020-04-03 苏州久显新材料有限公司 Spirobenzanthrone derivatives and electronic devices

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114075117A (en) * 2021-06-04 2022-02-22 陕西莱特迈思光电材料有限公司 Organic compound, and electronic element and electronic device using same
CN114075117B (en) * 2021-06-04 2023-07-21 陕西莱特迈思光电材料有限公司 Organic compound, and electronic element and electronic device using same
WO2023008708A1 (en) * 2021-07-27 2023-02-02 주식회사 로오딘 Organic light-emitting diode

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